How do I prevent cloth from being blown through an object?
I add an answer to be able to post my example (as I intended yours) that seems to work, and I guess does what you wish:



As said I pretty much used default values for all, except wind force...
Of course I have an example, very simple, setup but this may give you an Idea of what's not working. Maybe you can provide a better example for us to check?

And here you have the file to experiment, hth: